Frenchmans Lookout

Frenchmans Lookout is not your average Frenchman. In fact, it’s not a Frenchman at all. Located high above the West End of Tortola in the British Virgin Islands, this is the crash pad of the very well-heeled. Just ask Kate Moss, who gushes that it’s her favorite place in the Caribbean. After all, what’s not to like? The 10,000-square-foot private villa – yes, you read that right – has bi-level wrap-around decks and commanding views of the U.S. Virgin Islands. It’s pure paradise.

The Buzzword: Chartering

Chartering is the buzzword in these parts, from renting a private plane to get to Tortola via San Juan, to renting a private boat once you’re on the island. Chartering may sound pricey, but it can be the economical choice for groups of five and up. The commercial flights are on American, or the smaller carriers, Cape Air and Sunshine Air, which leave from San Juan. Caribbean charters are notorious for cutting corners on service and safety, so choose wisely. One of the most reputable companies is Fly BVI. These guys have their act together in safety, pilot experience, and plane maintenance. Clients include Jay-Z, Beyonce, and Richard Branson and his family. Branson is a commercial pilot, so if Fly BVI is good enough for him, you know you’re in good hands.

The real advantage to a charter, besides having a plane at your disposal, is getting to cut all the lines. You can arrange for VIP escort through the airport if you’re checking luggage, or head directly to your gate on the lower level without having to go through security again. Once you get to the plane, cold Red Stripes await for the 45-minute flight to Tortola. When you arrive, you’ll be escorted by another handler through the immigration line. For the competitive price and VIP service, charter flights are the way to roll.

Welcome to Paradise

Frenchmans Lookout recently became part of Inspirato, a membership-based, luxury vacation rental company with properties around the world. You pay an initiation fee of $15K, but then get to stay in villas across the globe, starting from a few hundred dollars a night. When you’re with family, friends or an entourage, it can work out economically in your favor if you travel a few times a year. Frenchmans Lookout is priced from $695/night; averaged over five beds/five baths, it comes to $140/room per night, which is unheard of for a luxury property. And, Frenchmans Lookout is even more stunning in reality than it is in the stunning pictures on Inspirato’s website. It’s a large villa – and by large, we mean 10,000 square feet – with two levels of wrap-around decks. The home looks like a sugar plantation; it was originally built by the creator of Dungeons & Dragons. It’s the furthest thing from a dungeon, though; dozens of French doors frame the house.

The home invites you to relax, with each corner on the first and second floors outfitted with hammocks and chill-out spaces overlooking the water. Wireless works perfectly throughout the property for those who feel the need to multi-task.

The common spaces are a major draw, from the “wish-I-had-this-at-home”gourmet kitchen, large dining room where you can hang out late into the night, and the outdoor dining and pool areas. In short, the villa is a destination unto itself.

The Logistics

Frenchmans Lookout is in Soper’s Hole, at the west end of Tortola. From Beef Island Airport, it’s a forty-minute drive. If you’re planning to go to the Last Resort, a popular island shack, make it your first stop from the airport for lunch.

Inspirato will stock your house with groceries and your choice of beverages. There’s usually a reserve of rum and other liquors that have been left over from previous guests, but no guarantees. The restaurant scene in Tortola is generally mediocre but for a handful of places. The main draw on the island is to spend your days boating and your evenings with your private chef or making a big family feast together. Most of the stores carry frozen meats and bleak products, so it’s best to pre-arrange with the Inspirato team to get higher-quality groceries upon arrival.

The villa can arrange for car rental during your stay, while in the evening, private driver is the way to go. Duncan (see sidebar) will hook you up and professionally navigate the dark roads so you can enjoy the interesting Tortola nightlife (more on that later). Transportation is expensive in general and is charged per person, not per car. Budget around $20–30 per person if you’re heading to any of the restaurants and clubs. Also, keep in mind that Tortola is quite British when it comes to punctuality – they’re not on “island time” here.

Whatever Floats your Boat

Frenchmans Lookout can arrange for boating day trips to explore the surrounding area. Boating and sailing are the major draw of Tortola – but these are not calm Caribbean waters. Currents are rough, so make sure that you get an experienced captain and a boat that’s at least 32 feet, if not larger. Tortola is centrally located, and from here you can explore Virgin Gorda, Peter Island, and Scrub Island, just to name a few. Neckar Island, Richard Branson’s private abode, is nearby, where you can arrange for lunch – but this will take pre-planning and lots of connections.

Virgin Gorda is a must if you’re in the area, starting with Little Dix Bay for lunch. Little Dix is part of the Rosewood collection, and it’s the Caribbean you dream of, with a small sandy alcove, thatched-roof umbrellas, and young and affluent jetsetters. Rooms are on the smaller side, but common areas are a homerun.

About 10 minutes from Little Dix are the Virgin Gorda Baths. You can climb these natural rock formations until you reach a salt-water pool that’s so calm you’ll feel like you’re the only person left in the world. To get to the Baths, you’ll anchor about 300 feet away and jump into the Caribbean, swimming to shore. From there, it’s a barefoot hike in bathing suits through rock terrain and shallow pools of water. While it’s the most-visited sight in Virgin Gorda, if you get there in the late afternoon, the crowds will have subsided and it’ll be a more pleasant experience.

No day on a boat is complete without a last stop at William Thornton, better known as Willy T’s, near Norman Island. A stand-alone floating restaurant and bar, it’s the epicenter of debauchery – day and night. As you dance up a storm, you’ll see the bare backsides of patrons as they jump off the roof for a public skinny dip. No, it’s not a special occasion – just another day at Willy T’s. Since this is a PG-13 show, the pictures say a thousand words: http://www.williamthornton.com/. To miss Willy T’s is like missing the Acropolis in Greece. OK, maybe that’s an exaggeration, but it’s a very worthwhile stop.

Beach Day

Smuggler’s Cove is the most beautiful beach in Tortola. If you get tired of boating, explore the island by car and spend the day drinking piña coladas and swimming in the Caribbean waters. Sebastian’s is a simple Caribbean spot for post-beach drinks and snacks. The menu is heavy on grilled lobster and other shellfish, and there’s a DJ during peak season and weekends.

The Cuisine Scene

For a low-key meal and drinks near the villa, head to Jolly Roger. Keep in mind that the New York dinner time of 9pm doesn’t work in Tortola – most of the kitchens are closed by then. It’s best to make reservations for dinner; restaurants are fully booked during peak times and your charming mug may not be enough to get you a table. The Dove and the Sugar Mill are the best restaurants in Tortola, but don’t expect Michelin to award stars anytime soon. Cuisine is upscale island fare – grilled fish, chops, and Caribbean specialties like coconut rice and conch fritters.

The Bananakeet is a visitors’ favorite, but less gourmet than the Dove and Sugar Mill.

It’s the view that’s spectacular: Bananakeet sits on a hill and during the day, the Caribbean stretches before you as far as the eye can see, while in the evening, the moon reflects on the dark water.

Tortola is for Swingers

There’s something about Tortola that seems to give everyone island fever. During a full moon, the place to be is Bomba, which inspires people to engage in wild, cocktail-fueled dancing, the flashing of flesh – and other unmentionable acts.

On other nights, the scene is at Quito’s Gazebo, which features a live reggae band. Sure, it’s a little disturbing to watch adults (some of whom may look like your 8th-grade science teacher) gettin’ jiggy with it, but it’s all part of the cultural experience. And, what happens in Tortola, stays in Tortola.